UPDATE: Want to know what these events are like? Check out my Match.com Stir Review. I even have a photo and video from an event I attended. –Russ

On one of my many Match.com dates – this one a few years ago – while chatting about the subject of online dating, one of my dates had a clever idea: “I want to message a bunch of people on Match.com, and invite them to a bar for a meetup. Not speed dating, just a bunch of single people getting dates.” I thought it was a great idea, but of course, neither of us ended up doing anything about it. Fortunately, we didn’t have to. Continue reading ‘Match.com ‘Stir’ Events Advice’ »

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Instant Messaging is great. You can chat with a number of friends, all at the same time, while doing work, watching TV, or reading on the web.

Admittedly, I honed my online dating chops, chatting with random girls on AOL in the late 90’s. There’s something great about talking in real-time, but still getting to think about what you’re going to say next.

So, since IMing is so great, pretty much every online dating site – including Match.com – has an Instant Messaging feature. It makes perfect sense, right? So, what’s the best way to use this feature to get dates online. Continue reading ‘Instant Messaging tips for online dating’ »

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If you want to have any success in online dating, you’d better have good profile photos. No matter how well you’ve written your online dating profile, having good photos will make sure more matches click through to your profile, give you winks, respond to your messages, and ultimately date you. So, here’s why your photos won’t do those things for you. Continue reading ‘7 Reasons Your Online Dating Profile Photo Sucks’ »

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I’ve told you plenty about what you should do with your online dating profile; but here’s some don’ts. These mostly apply to the guys, but ladies, watch out for some of this stuff, too. Continue reading ‘Top 10 Mistakes in Online Dating Profiles’ »


Writing an online dating profile is the most daunting part of online dating; but there’s little else so critical to your success. Since it is such a challenge, it’s no surpise that many profiles are clearly given very little thought – either by being incredibly short, non-descript, or downright cliché.

It’s no wonder why so many profiles begin to the tune of “it’s so hard to write about yourself,” but understanding yourself well enough to create a profile that represents you well is a healthy process. With a little guidance, your online dating profile can stand out from the millions of others to present the interesting you. A well-written profile will not only ensure that you receive responses when you make first contact; but will attract and motivate potential matches into contacting you – making your online dating experience easier, more enjoyable, and more successful. Continue reading ‘How to write an online dating profile’ »


So, you’ve mined the conversation nuggets from your target’s profile, you’ve sent short, funny, and brilliant one-line hook, and boom, you’ve gotten a response. Now what? This is a very critical point in the online dating process, but this is the final step before meeting in person. This is “the kill,” if you will: the second message with an online dating prospect.

A high-value woman has an incredible volume of messages to manage. The fact you’ve gotten a response speaks to your online dating acumen. But because this woman has such volume to manage, you can’t waste time. You need to meet her as soon as possible. Additionally, you want to ensure that she is who you think she is without investing more time. So, you should have two goals for this online dating message: maintain interest, and secure a date. Continue reading ‘Follow-up Online Dating Message Advice’ »


OkCupid has conducted an interesting study regarding response rates based upon specific key words used in opening online dating messages.

Pretty fascinating, huh?

Continue reading ‘What to say in a first online dating message’ »

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A female reader forwarded to me this incredible match.com message.

I just wanted to say 'thanks' for completely ignoring my previous email. It must be tough on you to have such an overinflated sense of self-importance. I guess being deluged with emails from guys who you think you are better than can get to be a hassle, huh? But you don't even have the courtesy to send back a polite 'no thanks?' I guess that's how you were raised. Best of luck to you in your search :)

Wow. The most entertaining thing is that this e-mail’s subject is “2nd attempt,” as if such an attack could be considered an “attempt” to win a woman over. Continue reading ‘How NOT to Write an Online Dating Message’ »


There’s one very simple piece of advice you can follow to improve your online dating profile, and profile photos, and online dating messages tremendously: inject all of them with as many conversation nuggets as you possibly can.

  • What is a conversation nugget? Simply, something specific and potentially interesting that can be the subject of a conversation.
  • How can I start using conversation nuggets? For everything you have in your profile, photos, or messages, ask yourself “how could this start a conversation?”
    • Instead of the photo of you with a bunch of random friends, share the photo of you drinking a gigantic beer at Oktoberfest.
    • Instead of saying in your profile that you like Indian Food, name which restaurant is your favorite. Instead of saying that you’re thinking of getting a dog, say what breed you plan to get and why. Better yet, pose the question right in your profile: “should I get a Beagle or a Boston Terrier?”
    • Instead of sending a message to a match asking her about her proclaimed nutrition expertise, tell her you just ate a bunch of broccoli, and you swear you can feel the detoxifying enzymes in your body ask, “is this possible?” in one-line hook form.

Continue reading ‘Conversation Nuggets in Online Dating’ »

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So, you’ve made first contact with someone of interest (hopefully you used the who’s viewed me shuffle and/or the one-line hook), and now you want to go on a date with them. Here are a few guidelines on how to do that. First of all, it’s better to meet very early on than to let things drag on by chatting on IM or the phone for a long time. The good girls can go very fast, things can fizzle out fast online, and you never know who will disappoint you when you meet in person, so it’s best to get right to it. Things will vary from social group to social group, but in late 20’s to early 30’s in a major metropolitan area, I have always met within a few e-mails. My typical progression may go like this:

Building Interest With First Contact

For reference, imagine there’s a girl who has cleverly put in her profile: “I’m new to town, are there any good Thai restaurants here?” (You should put conversation nuggets like this in your profile). My one-line hook message might look like this:

Are you still looking for great Thai food? I looked for the longest time, but I finally tried a place called Tiparo’s on Clark street, and it was great! They have the best pumpkin curry I’ve had since my days in SF. Have you tried that place yet?


That’s a pretty long first message, probably more appropriate if you’ve elicited a wink using the who’s viewed me shuffle, but here’s a little breakdown:

  • I’ve shown that I’m paying attention by referring to something from her profile.
  • I’ve spoken of specifics: (or conversation nuggets) a specific restaurant, a specific dish. This makes the conversation richer so there’s more for her to respond to. “Pumpkin Curry” is way more interesting than “good food.” I even threw a city that I have experience with just in case she has interest in talking about that.
  • I’ve ended with a question and stayed on one subject. The message is easy to respond to: there’s only two total questions, both about Thai restaurants. Yet, the message is rich with specifics that she can use to open other conversation threads.
  • I’ve set up some good fodder for a date idea. You can bet that if we go out to eat, we’ll try a Thai place.

So hypothetically, let’s say she responds like this:

Good to hear from you, Russ! Yes, I have finally gotten settled in, and found a good Thai place, but I haven’t tried Tiparo’s yet. I really like Pot Pan – it’s right down the street from my house, so I go there often. They don’t have Pumpkin Curry, though – that sounds soooo good!

SF is my favorite city. Have you ever tried the Japanese Ramen place there called Katana Ya? I wish I had known in my college days that Ramen could be that good :P Why did you move?


Awesome. Exactly what we want. Not only is she glad to hear from us, we’ve found common ground with her: Thai food, San Francisco (we have tried that restaurant), she wants to try this Pumpkin Curry, and she wants to know more about us.

Making it Easy

At this point, we haven’t built a ton of rapport with her, so we may be more comfortable sending a message without a date request; but if you’ve gotten this much enthusiasm, strike while the iron is hot:

Good to meet you, Rachel. YES, as a matter of fact, I have gone to Katana Ya. I used to eat lunch there at least once a week. Wow, you have me craving Ramen now (unfortunately, not the kind you can get at the corner store).

My move is a long exciting story (and I have to leave some mystery, you know :P) but I just love this city and I wanted to try something new. Do you want to get a drink with me this week? I’m free Tuesday and Wednesday night at 8pm. Have you been to Beachwood Inn before? We could meet there since it’s in your area. Let me know what works for you, or feel free to give me a call at 402-555-1234.


So, in this message, I have dug deeper into the conversation thread by responding to some of the elements she had in her previous message. I’ve told her a little bit about her question, but I’ve been playful and left some conversation for when we meet later. Finally I’ve made a great request for a date. Notice these points:

  • I’ve picked a place that’s convenient for her. Wow, I’m listening to her, and making it easy for her to meet me. I extrapolated from the restaurant she said she lived near what neighborhood she lives in. If I don’t know of a place there, I can check Yelp.com to find a place with a good atmosphere for conversation.
  • I’ve been specific with times and dates, and I’ve given two options so we have less back-and-forth trying to get our schedules to match up.

We are making it very easy for her to decide on this. A beautiful girl has dozens, if not hundreds, of e-mails from guys. Think of how much easier it is to respond to this than “wanna hang out sometime?” Notice that I have gently offered up my phone number. This is a little gutsy, and it may be wiser to wait to give that until after I’ve gotten a date confirmation (“if you need to get in touch, give me a call at…”). You’re a busy guy with lots of dates, and you don’t want strange girls calling you any more than she wants strange guys doing so. I’ve been bold and offered it up here just to make setting a date easier.

Notice that I used our shared interest in Thai food to build rapport, but I didn’t suggest it for a first date. Your style may turn out differently, but I like to save dinner for the second date. I like to just get a drink to see how we get along and make sure she’s who I thought she was. So, I’m managing this risk by suggesting a date that can be as short, or as long, as we wish. Also note, that I didn’t ask for a Friday, a Saturday, or even a Thursday for a date. That’s valuable social real estate, and if it isn’t taken up on your calendar, it is taken up on a beautiful woman’s.

Also, because our first messages were about Thai food, we have the idea of a Thai dinner floating around in both of our heads to keep us excited for the next date (not to mention another easy decision).

So, meet as soon as possible, and make it as easy as possible for her to accept the date by picking a convenient place, specific times and dates, and at least two options. Following these tips along with a strong profile, and good first contact strategies should make securing dates a breeze.

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I got a really great question from one of you folks about rejection.

I don’t like rejection, either receiving or dishing it out, but the latter a lot more so. If a woman winks and you’re not interested how should you deal with it?  Click “not interested”, send a message or just ignore it?

What about if you get to date level and you’re not interested?  Do you tell them there and then? Message them later? You were talking about doing 2-3 dates a week if you can, but that’s a lot of dishing out rejections.  How do you do that without just hurting a lot of people?  I’ve had one date of match and having to tell her not interested afterwards made me avoid the site for a while afterwards!

First of all, I don’t know if anyone likes rejecting people – or being rejected for that matter, but it’s a fact of life. Here’s a few guidelines.

  • Online, just ignore. In my experience, it’s perfectly acceptable on Match.com to just ignore the winks and messages of those you aren’t interested in. In my many years using the site, I’ve only gotten the “not interested” a couple of times – but I’ve been ignored plenty of times! Keep in mind that there are tons of reasons why someone may not respond; and if it’s because they aren’t interested, don’t fret, you weren’t compatible anyway. Some people are more comfortable sending the “not interested,” and that’s perfectly acceptable too – if you’re comfortable with it.
  • Manage expectations. Make it very clear that you are really actively dating, and that you’re determined to find just what you’re looking for. You don’t have to say this explicitly, though. I like to bring up the topic of our experiences with the site, trading stories a bit. This can make them less likely to assume that you’ll be interested. And if you are interested, it will make you more desirable to show that you’re active. This works better in the larger cities, where there is a larger pool, and it’s fairly obvious that there won’t be a second date unless there’s a pretty strong spark.
  • Open a dialogue. Sometimes, even when I am interested, I like to say something like “hmm…so, what do you think of this?” to open up a dialogue so we can openly share with each other our observations. Be open about what you see as good, and what has you wondering. If you’re lighthearted about it, it can actually make the date more comfortable.
  • Don’t look at it as rejection. Usually, it’s pretty obvious to both parties early on if it isn’t going to work out. Sometimes, “it’s not me or you – it’s us.” You should never feel bad about yourself if someone isn’t interested in you. Ultimately, you want someone who excites you, and who is excited about you – and you should never settle for less than that.

Honestly, if someone doesn’t have a grasp of what I think is usually fairly obvious, I have given, and received, the notorious “I’ll call you.” Everyone hates this, but these days everyone gets the picture. I personally think this, or simply not returning calls, is okay if things haven’t progressed…um…physically (when dating online). Beyond that, you do need to be open and honest: if you’ve gotten that far, then hopefully you have clear communication.

So, there’s my take on it, but I know opinions will differ. I’m really interested to hear what you guys think?

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Able to get a response to your online dating e-mails, but don’t know what to do next? I’ll talk about that in this video:

Note that I talk about the one-line hook for writing a great first online dating message.

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Here’s a video demonstrating the “Who’s Viewed Me” Shuffle, a Match.com searching technique that will get women to wink at you, thus conserving your resources and getting her to express interest in you. This puts you in a more favorable position when writing that first message.


I get a lot of questions from faithful readers about Match.com’s “Wink” feature. Is it okay to use? What do you do if someone winks at you? What if you wink at someone and they don’t wink back?

For the guys, let me summarize it with this photo:


Well, that’s really simplifying it, but I’ll get more into that in a second. Continue reading ‘Match Winks: an Overview’ »


Ross Felix, a commenter on David Evan’s blog, Online Dating Insider, brought up an excellent point:

Match.com 15 mil users / 1.32 million premium members = 91% of the people can’t reply to your email without upgrading their membership.

That’s right, if you didn’t get a response to the last message you sent out to another Match.com member, don’t take it personally: 91% of the users are unable to respond to you. Wow. I’m surprised it’s that high of a rate.

Maybe I’m surprised, because I know that if you try to get winks on Match.com first, and limit the energy you expend when you do write messages on Match.com, you will have much better odds. There may be a small percentage of members who can write you back, but Match is still the best dating site, IMO.

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